New simple syntheses of (E)-1-azido- (or thiocyanato)-alk-1-enes from alk-1-ynes by hydroboration

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 6, 1998, Pages 1013-1014

  Masuda, Yuzuru ^a   Murata, Miki ^a   Ikeda, Minehito ^a   Watanabe, Shinji ^a  

^a KITAMI INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748608002     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a708932e     Document Type: Article

References (24)

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10. G. W. Kabalka, T. M. Shoup and N. G. Goudgaon, Tetrahedron Lett., 1989, 1483.
11. For general synthesis and application of 2-azidoalk-1-enes [except for (E)-1-azido-3,3-dimethylbut-1-ene] via iodoalkyl azides see (a) F. W. Fowler, A. Hassner and L. A. Levy, J. Am. Chem. Soc., 1967, 89, 2077;
12. A. Hassner and F. W. Fowler, J. Org. Chem., 1968, 33, 2686;
13. (b) A. Hassner and F. W. Fowler, Tetrahedron Lett., 1967, 1545;
14. J. Am. Chem. Soc., 1968, 90, 2869;
15. J. Org. Chem., 1986, 51, 3176;
16. A. Hassner, B. A. Belinka, Jr., M. Haber and P. Munger, Tetrahedron Lett., 1981, 22, 1863;
17. Y. Nomura, Y. Takeuchi, S. Tomoda and M. M. Ito, Bull. Chem. Soc. Jpn., 1981, 54, 261.
18. (a) K. Tamao, T. Kakui and M. Kumada, Tetrahedron Lett., 1980, 111;
19. (b) It has been shown that the formation of (E)-β-thiocyanatostyrene from 1-chloro-1-phenyl-2-thiocyanatoethane, itself derived from styrene, is possible: R. G. Guy and I. Pearson, Bull. Chem. Soc. Jpn., 1976, 49, 2310.
20. (a) S. Tomoda, Y. Matsumoto, Y. Takeuchi and Y. Nomura, Bull. Chem. Soc. Jpn., 1986, 59, 3283;
21. 3, have been formed through the azido alcohol or the vinyl chloride: R. E. Bolton, C. J. Moody, M. Pass, C. W. Rees and G. Tojo, J. Chem. Soc., Perkin Trans. 1, 1988, 2491;
22. A. L. Beck, W. J. Coates and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1990, 689.
23. (a) T. K. Chakraborty and G. W. Reddy, Tetrahedron Lett., 1990, 1335;
24. (b) It is reported that formation of (E)-β-azidostyrene from 1-bromo-1-phenyl-2-azidoethane, itself derived from styrene, is possible: A. Hassner, F. P. Boerwinkle and A. B. Levy, J. Am. Chem. Soc., 1970, 92, 4879.